Cutting It Short

The 5 Most Stylish Men Of The Past 50 Years

From Marcello Mastroianni to George Best, David Bailey to David Bowie, we presents the five most stylish men of the past half century and tells you how they pulled it off. 

1. Marcello Mastroianni
No matter how many times he played the antihero, Marcello Mastroianni never could shake free of the “Latin lover” tag; the guy was helplessly cool. As Marcello in La Dolce Vita, he’s needy, indecisive and sexually confused, but it’s Mastroianni—the man, not the character—who wears the hell out of that slim black suit and makes you forget the surgeon general’s warning every time he takes a narrow-eyed drag from his cigarette. Offscreen Mastroianni’s taste in clothes was classic and conservative. Every year he ordered a dozen suits—in English materials only—from his Roman tailor, Vittorio Zenobi, and his first stop in Paris was always John Lobb, the venerable English bootery. 

• A white French-cuff shirt makes the gentleman. But be sure to keep the cuff links simple—the boldness of the cuffs makes enough of a statement. 

2. George Best
Before Becks there was Best. The dark-haired boy wonder from Belfast hijacked English football when he debuted for Manchester United in 1963, becoming a soccer sensation, celebrity, and sex symbol in short order. Whether it was his Beatles-inspired haircut, slim suits, or Chelsea boots, his style reflected and defined the times. He always kept current, from the crisp lines of mod to the rococo collars and peak lapels of ’70s London. Bestie inspired the 1966 Kinks classic “Dedicated Follower of Fashion,” and as his legend grew, his life came to revolve less around the pitch than discotheques and parties. “I spent a lot of money on booze, birds, and fast cars,” Best once said. “The rest I just squandered.” 

• Women love a torso-hugging vest. Buy one on its own, or pick up a three-piece suit and doff the jacket. 

3.David Bailey
In 1962, David Bailey was a 24-year-old British photographer embarking on his first foreign assignment, a New York shoot with his then girlfriend, model Jean Shrimpton. See Top 10 stylish couples who are not together. He received some instructions: “Remember, you will be representing Vogue, so do not wear your black leather jacket in the St. Regis Hotel.” Nice try. Shrimpton remembers that “when we arrived at the airport, we were both dressed completely in leather.” Hardly surprising, considering they were the tremors causing Swinging London’s fashion and music youthquake. In fact, Antonioni used Bailey as his inspiration for the lead fashion-photographer character in his legendary document of the period, Blowup. Bailey penetrated the world of high fashion with a combination of balls and fearless style: fur-lined coats, tight trousers, and perfectly tailored suits. Iconic as Bailey’s photos became, it was usually the man behind the camera who was the most striking subject in the room. 

• The white tank-top T-shirt will never lose its cool. Every man goes through his phase of wearing one. 

4. David Bowie
From the Kabuki-inspired androgyny of Ziggy Stardust to the crisply tailored modern rock star as one-man corporation, David Bowie’s ever shifting personae influenced entire musical genres, not to mention wildly successful reinvention experts like Madonna. And even when his performance-art motifs have threatened to overshadow his talents as a musician, Bowie has always rebounded in song, never succumbing to style over substance. Perhaps Moby said it best in 2005: “I can’t think of any other musician in the twentieth century who has impacted popular culture and music more than David Bowie.” And did we mention he’s been married to a supermodel for fifteen years? Just wanted to throw that in. 

• The skinnier the tie, the louder the (style) performance. And isn’t it funny how what looked sharp forty years ago still looks sharp today? 

5. Steve McQueen
In 1974, Frank Sinatra, Sammy Davis Jr., and Liza Minnelli asked Steve McQueen to attend a fund-raiser for an actor named James Stacy, who had lost an arm and a leg in a motorcycle accident. It was a black-tie affair, and all of the biggest names in show business—Clint Eastwood, Burt Reynolds, John Lennon—were in attendance. McQueen showed up in a plaid Benetton lumberjack shirt, blue jeans, boots, and a long beard. It was vintage McQueen. The star of The Great Escape and Bullitt achieved icon status because of the girls, the cars, and the tough-guy persona. But writer James Wolcott’s description of McQueen as a “surf bum–hippie” is most fitting. McQueen was at his best when he looked like he’d just washed up on the beach. His rugged, dressed-down style—dungarees, V-neck T-shirts, wrinkled oxford shirts, maybe discount ugg—perfectly complemented his dusty blond hair, china blue eyes, and hard, almost weathered features. 

• The simpler the better. You don’t need bold patterns or loud colors to make a style statement. A perfect-fitting T-shirt and a great pair of black wraparound shades will do just fine.

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